Chokoloskee Island Vacation Packages 2025/2026 from $412

Chokoloskee Island flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Home2 Suites by Hilton Fort Myers Airport

Save 100% on your flight

$412

per person

Jan 25 - Jan 30

found 11 hours ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Matanzas Inn Bayside Resort and Marina

$505

per person

Jan 25 - Jan 30

found 13 hours ago

Roundtrip flight included

Detroit (DTW) to Fort Myers (RSW)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free self parking and free WiFi. A terrace, a picnic area, and luggage storage are also on offer.

The Perry Hotel Naples

Save 100% on your flight

$1,188

per person

Jan 20 - Jan 27

found 19 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and a beach shuttle. Relax with a drink at one of the 2 bars/lounges and enjoy the a rooftop terrace.

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach

Save 100% on your flight

$2,481

per person

Jan 20 - Jan 27

found 19 hours ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This luxury resort features a private beach, a full-service spa, and 2 restaurants. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the outdoor pool and visit the 2 bars/lounges and beach bar for drinks.

South Seas Resort

Save 100% on your flight

$951

per person

Dec 17 - Dec 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

This smoke-free resort features a private beach, a golf course, and a water park. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Bring the family and enjoy the children's pool, waterslide, and kid-friendly dining.

Top Chokoloskee Island hotels deals

Deep Water Access with a Panoramic View of Chokoloskee Bay

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This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

The Ultimate Fishing Retreat- Comfortable and Convenient!

$423 nightly

$464 total

Nov 10 - Nov 11

Total with taxes and fees

This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Waterfront RV with Boat Slip in Chokoloske...Surrounded by Everglades Nat'l Park

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Enjoy laundry facilities and air conditioning. Popular attractions Smallwood Store and Chokoloskee Bay are located nearby.

Air conditioning

Laundry

Everglades Adventures Hotel Suites by Ivey House

107 Camellia St E, Everglades City, FL

Free Cancellation

Reserve now, pay when you stay

$129 nightly

$143 total

Nov 16 - Nov 17

Total with taxes and fees

An outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Luggage storage is also provided.

Pool

Parking included

Port of the Islands Everglades Adventure Resort

$145 nightly

$162 total

Nov 10 - Nov 11

Total with taxes and fees

A marina and an outdoor pool are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Parking included

Captain's Table Hotel

202 Broadway Ave E, Everglades City, FL

Free Cancellation

Reserve now, pay when you stay

$78 nightly

$87 total

Dec 10 - Dec 11

Total with taxes and fees

An outdoor pool, free self parking, and laundry facilities are featured at this hotel. A computer station and luggage storage are also provided.

Pool

Parking included

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Smallwood Store

You can spend time exploring the galleries in Smallwood Store during your trip to Chokoloskee. You can seek out the fishing spots while in the area.

Frequently asked questions

How much are vacation packages to Chokoloskee Island?

$412 is all you need to spend for a memorable vacation in Chokoloskee Island. Bundle your flights and hotel into a vacation package with Travelocity and see how much the savings start to grow. With prices as good as these, it's never been easier to travel!

Where can I get the best vacation package deals for Chokoloskee Island?

You'll discover a tempting selection of Chokoloskee Island package deals on Travelocity. With 400 partner airlines and 1,000,000 properties worldwide, crafting your ideal vacation will be simple.

Why should I purchase my Chokoloskee Island vacation package via Travelocity?

From our 24/7 support to our range of incredible destinations, we're committed to fulfilling your travel dreams. All you'll have to do is to click and book — our Price Match Guarantee will make sure you score the best price.

Will I save money on my Chokoloskee Island car rental if I combine it with hotels and flights?

Bundling your bookings into a Chokoloskee Island vacation package will leave you with a nice chunk of spare change. You can combine a car and flight; a hotel, flight and car; or a car and hotel. There's no better way to discover the greater Chokoloskee Island area than from the comfort of your own rental car. You can also add activities and experiences to your Travelocity package.

Which airport is best for Chokoloskee Island?

Choose from Southwest Florida Intl. Airport (RSW) or Naples Municipal Airport (APF). They are the major airports for people flying in and out of Chokoloskee Island.